Hydrochloric Acid → 4-[(6a-Methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoic acid

HRID 1097393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097393
[CH3:1][C:2]12[C:14]3[C:6](=[CH:7][C:8]([NH:15][C:16]4[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=4)=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]1)[CH2:5][CH2:4][CH2:3]2.[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]12[C:14]3[C:10](=[CH:9][C:8]([NH:15][C:16]4[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=4)=[CH:7][C:6]=3[CH2:5][CH2:4][CH2:3]1)[CH2:11][CH2:12][CH2:13]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25190221Ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate

Produkt 1

HCID 251902204-[(6a-Methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoic acidAusbeute 80,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.250 g) in ethanol (15 ml) was added with 20% aqueous sodium hydroxide (5 ml), and the mixture was stirred overnight at room temperature. The reaction mixture was made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from ethyl acetate-n-hexane to obtain the title compound (0.185 g, yield: 80%) as pale brown needles (melting point: 232-234° C.).

Aufarbeitung

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customthe resulting residue was recrystallized from ethyl acetate-n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a621ec11f7fc47beba1b58ef9589b914
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143260B2

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